A practical synthesis of tert-alkylamines via the Ritter reaction with chloroacetonitrile

Ritter reaction of tertiary alcohols with chloroacetonitrile and subsequent cleavage of chloroacetyl group in the resulting chloroacetamide with thiourea is an efficient procedure for synthesis of tert-alkylamines.

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Published inSynthesis (Stuttgart) no. 12; pp. 1709 - 1712
Main Authors Jirgensons, A, Kauss, Kalvinsh, Gold, MR
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2000
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Ritter reaction
amines
tertiary alcohols
amides
cleavage
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Abstract Ritter reaction of tertiary alcohols with chloroacetonitrile and subsequent cleavage of chloroacetyl group in the resulting chloroacetamide with thiourea is an efficient procedure for synthesis of tert-alkylamines.
AbstractList Ritter reaction of tertiary alcohols with chloroacetonitrile and subsequent cleavage of chloroacetyl group in the resulting chloroacetamide with thiourea is an efficient procedure for synthesis of tert-alkylamines.
Author Kauss
Gold, MR
Kalvinsh
Jirgensons, A
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Issue 12
Keywords Ritter reaction
amines
tertiary alcohols
amides
cleavage
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References HOHENLOHEOEHRIN.K (WOS:000165147200014.8) 1962
JIRGENSONS A (WOS:000165147200014.11)
KRIMEN LI (WOS:000165147200014.13) 1969; 17
JIRGENSONS A (WOS:000165147200014.10)
BISHOP, R (WOS:A1987G815800028) 1987; 28
Giardina, GAM (WOS:A1996VN22800013) 1996; 6
RITTER, JJ (WOS:A1948UB19600023) 1948; 70
RITTER, JJ (WOS:A1952UB41400053) 1952; 74
RITTER, JJ (WOS:A1948UB19600022) 1948; 70
PETERI, D (WOS:A1973P428800020) 1973; 23
CHRISTOL, H (WOS:A19616550A00014) 1961
STILL, WC (WOS:A1978FF16900041) 1978; 43
MASAKI, M (WOS:A1968B530900086) 1968; 90
STEGLICH, W (WOS:A1971I475400018) 1971; 10
CHRISTOL, H (WOS:A19616550A00013) 1961
BISHOP R (WOS:000165147200014.3) 1991; 6
KOPKA, IE (WOS:A1980KQ10000014) 1980; 45
FONTANA A (WOS:000165147200014.6) 1968; 98
ALLMENDINGER, T (WOS:A1988M582100012) 1988; 71
ICHIKAWA, Y (WOS:A1990DV84900027) 1990
References_xml – volume: 74
  start-page: 763
  year: 1952
  ident: WOS:A1952UB41400053
  article-title: N-ACYL-BETA-PHENETHYLAMINES, AND A NEW ISOQUINOLINE SYNTHESIS
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: RITTER, JJ
– volume: 90
  start-page: 4508
  year: 1968
  ident: WOS:A1968B530900086
  article-title: A NEW METHOD FOR REMOVAL OF CHLOROACETYL GROUPS
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: MASAKI, M
– start-page: 2319
  year: 1961
  ident: WOS:A19616550A00014
  article-title: TRANSPOSITIONS ACIDOCATALYSEES .11. REACTION DE RITTER SUR ALCOOLS BENZYLIQUES TERTIAIRES
  publication-title: BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE
  contributor:
    fullname: CHRISTOL, H
– volume: 6
  start-page: 261
  year: 1991
  ident: WOS:000165147200014.3
  publication-title: COMPREHENSIVE ORGANI
  contributor:
    fullname: BISHOP R
– volume: 45
  start-page: 4616
  year: 1980
  ident: WOS:A1980KQ10000014
  article-title: PREPARATION OF A SERIES OF HIGHLY HINDERED SECONDARY-AMINES, INCLUDING BIS(TRIETHYLCARBINYL)AMINE
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: KOPKA, IE
– volume: 70
  start-page: 4048
  year: 1948
  ident: WOS:A1948UB19600023
  article-title: A NEW REACTION OF NITRILES .2. SYNTHESIS OF TERT-CARBINAMINES
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: RITTER, JJ
– start-page: 645
  year: 1962
  ident: WOS:000165147200014.8
  publication-title: MONATSH CHEM
  contributor:
    fullname: HOHENLOHEOEHRIN.K
– start-page: 2313
  year: 1961
  ident: WOS:A19616550A00013
  article-title: TRANSPOSITIONS ACIDOCATALYSEES .10. REACTION DE RITTER SUR ALCOOLS BENZYLIQUES SECONDAIRES ET BENZYLCARBINOLS
  publication-title: BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE
  contributor:
    fullname: CHRISTOL, H
– volume: 23
  start-page: 577
  year: 1973
  ident: WOS:A1973P428800020
  article-title: CHEMISTRY AND TOXICOLOGY OF A NEW ANTIVIRAL SUBSTANCE N-(1-ADAMANTYL)-2-(2-DIMETHYLAMINO-ETHOXY)-ACETAMIDE-HCI .1.
  publication-title: ARZNEIMITTEL-FORSCHUNG/DRUG RESEARCH
  contributor:
    fullname: PETERI, D
– volume: 28
  start-page: 1585
  year: 1987
  ident: WOS:A1987G815800028
  article-title: RITTER REACTIONS .2. REDUCTIVE DEAMIDATION OF N-BRIDGEHEAD AMIDES
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: BISHOP, R
– ident: WOS:000165147200014.10
  publication-title: UNPUB
  contributor:
    fullname: JIRGENSONS A
– volume: 98
  start-page: 1261
  year: 1968
  ident: WOS:000165147200014.6
  publication-title: GAZZ CHIM ITAL
  contributor:
    fullname: FONTANA A
– volume: 10
  start-page: 75
  year: 1971
  ident: WOS:A1971I475400018
  article-title: REMOVAL OF CHLOROACETYL GROUP FROM N-CHLOROACETYL DERIVATIVES OF AMINO ACIDS AND PEPTIDES BY MEANS OF 1-PIPERIDINETHIO-CARBOXAMIDE
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  contributor:
    fullname: STEGLICH, W
– ident: WOS:000165147200014.11
  publication-title: IN PRESS EUR J MED C
  contributor:
    fullname: JIRGENSONS A
– volume: 6
  start-page: 2307
  year: 1996
  ident: WOS:A1996VN22800013
  article-title: A reliable and efficient synthesis of SR 142801
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  contributor:
    fullname: Giardina, GAM
– volume: 71
  start-page: 395
  year: 1988
  ident: WOS:A1988M582100012
  article-title: SYNTHESIS OF AN OPTICALLY-ACTIVE PENEM INTERMEDIATE BY ASYMMETRIC AMIDOALKYLATION
  publication-title: HELVETICA CHIMICA ACTA
  contributor:
    fullname: ALLMENDINGER, T
– start-page: 1347
  year: 1990
  ident: WOS:A1990DV84900027
  article-title: 1ST SYNTHESIS OF AMINOBISABOLENE
  publication-title: CHEMISTRY LETTERS
  contributor:
    fullname: ICHIKAWA, Y
– volume: 70
  start-page: 4045
  year: 1948
  ident: WOS:A1948UB19600022
  article-title: A NEW REACTION OF NITRILES .1. AMIDES FROM ALKENES AND MONONITRILES
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: RITTER, JJ
– volume: 43
  start-page: 2923
  year: 1978
  ident: WOS:A1978FF16900041
  article-title: RAPID CHROMATOGRAPHIC TECHNIQUE FOR PREPARATIVE SEPARATIONS WITH MODERATE RESOLUTION
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: STILL, WC
– volume: 17
  start-page: 213
  year: 1969
  ident: WOS:000165147200014.13
  publication-title: ORG REACTIONS
  contributor:
    fullname: KRIMEN LI
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Snippet Ritter reaction of tertiary alcohols with chloroacetonitrile and subsequent cleavage of chloroacetyl group in the resulting chloroacetamide with thiourea is an...
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Chemistry, Organic
Physical Sciences
Science & Technology
Title A practical synthesis of tert-alkylamines via the Ritter reaction with chloroacetonitrile
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